Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland.
J Org Chem. 2010 Mar 5;75(5):1740-3. doi: 10.1021/jo902167r.
This paper presents a simple and efficient route to chiral cis-6-substituted 2-(2-hydroxyethyl)-5,6-dihydro-2H-pyrans, a versatile chiral building block. The strategy is based on three key transformations: enantioselective hetero-Diels-Alder (HDA) reaction of aldehyde with Danishefsky's diene, selective reduction of carbonyl function, and Claisen or related rearrangement. The synthetic utility of the methodology is illustrated by total synthesis of antibiotic (-)-centolobine.
本文提出了一种简单高效的手性顺式-6-取代 2-(2-羟乙基)-5,6-二氢-2H-吡喃路线，这是一种多功能的手性构建块。该策略基于三个关键转化：醛与 Danishefsky 二烯的对映选择性杂 Diels-Alder (HDA) 反应、羰基功能的选择性还原以及 Claisen 或相关重排。该方法的合成实用性通过抗生素 (-)-centolobine 的全合成得到了说明。
